Going to Chicago for the first time in Late September and need advice

Question

. Landing to O’Hare and staying downtown in Hotel 71.

What are the absolute must sees and must eats? Any tour operators you recommend?

DO we need a car rental or should we take a cab from airport to hotel? How about cab or car for around the city?

We have only 3 nights/4 days.

Answer 1

take a cab. many museums downtown.

Answer 2

DEEP DISH PIZZA.  Gino's East is where it all started.  

Banderas is also a restaurant with good food.  I recommend taking a stroll along Lake Mich by the museums; you get a good view of the skyline.  The architecture boat tour is nice as well.  Millenium Park.  

I think car rental might be better if you can get a good rate.  If you know where to look, plenty of street parking.  O'Hare's like a 40-45 min drive to downtown Chicago.  

Answer 3

Try http://www.AmericaCheapHotels.com

Answer 4

I would definitely take a cab. There's always, always traffic, no matter what time of day or night it is, around O'Hare, and if you don't know what you're doing, it's stressful. Pay extra for a cab and relax. It'll probably be about $50 each way because it's pretty far from downtown. I would also use a cab for everything else. Parking is a nightmare anywhere downtown, and by the time you find a lot that has spaces available, or a parking spot, it's just not worth it, especially because valet and lots are expensive.

I would do one nice dinner at a steakhouse because that's what we're known for. I think the best one for people visiting from out-of-town is the Chicago Chop House. It's amazing, delicious steaks and has a very Chicago atmosphere, but not at all gimicky. Just be sure to make reservations before you go, it's pretty popular. You can make them online at their Web site.

I would definitely walk up and down Michigan Ave. It's mostly expensive store, but it's a really pretty street and shows you why Chicago is such a beautiful city. I still enjoy walking on it sometimes.

I don't know why you're visiting Chicago (couple's getaway, girl's weekend, just a relaxing visit), so it's hard to make recommendations otherwise. I would just explore and see where it takes you. Walk a lot (September will be great weather) and see the city that way. If you want to go up one of the observatory decks, I would recommend Hancock over Sears any day. Must better view and about half the cost, not to mention it's in a very convenient area (Off Michigan, near shopping).

Enjoy your trip. You'll love Chicago.